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Ribosylthymine
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Name

Ribosylthymine

 EINECS 215-973-9
CAS No. 1463-10-1 Density 1.576 g/cm3
PSA 124.78000 LogP -2.54350
Solubility N/A Melting Point 183-184 °C(lit.)
Formula C10H14N2O6 Boiling Point N/A
Molecular Weight 258.231 Flash Point N/A
Transport Information N/A Appearance white powder
Safety 24/25 Risk Codes 26/27/28
Molecular Structure Molecular Structure of 1463-10-1 (5-Methyluridine) Hazard Symbols VeryT+
Synonyms

1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;Uridine,5-methyl-;5-Methyl uridine;Thymine riboside;Methyluridine;5-Methyluridin, Ribothymidine;

Article Data 71

Ribosylthymine Synthetic route

3180-76-5

2',3',5'-tri-O-benzoyluridine

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With sodium methylate In methanol98%
With ammonia In methanol for 96h;98%
With sodium methylate In methanol for 0.5h; Heating;93%
3180-76-5

2',3',5'-tri-O-benzoyluridine

A

93-89-0

benzoic acid ethyl ester

B

55-21-0

benzamide

C

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With ammonia In ethanol at 20℃;A n/a
B n/a
C 95%
101796-28-5

1-(5'-O-trityl-β-D-ribofuranosyl)thymine

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With carbon tetrabromide In methanol at 20℃; for 12h; Irradiation;94%
With sulfuric acid; water; silica gel In acetonitrile at 25℃; for 0.283333h;93%
119794-52-4

1-[5'-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 5.3h;93%
3650-91-7

3-Methylthymidin

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction;88%
87817-95-6

2',3'-O-isopropylidene-5'-O-methoxymethyl-5-methyluridine

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With trifluoroacetic acid for 19h; Ambient temperature;87%
144490-03-9

1,2,3,5-tetra-O-acetyl-β-L-ribofuranose

7288-28-0

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
Stage #1: 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose; 2,4-bis(trimethylsiloxy)-5-methylpyrimidine With tin(IV) chloride In dichloromethane for 12h; Reflux;
Stage #2: With acetic acid In dichloromethane at 20℃; for 1h;
Stage #3: With ammonia In methanol at 20℃; for 12h;		85.06%
65-71-4

thymin

118-00-3

G

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With purine nucleoside phosphorylase; uridine phosphorylase at 90℃; for 48h; pH=9; aq. phosphate buffer; Enzymatic reaction;85%
In water; dimethyl sulfoxide at 25℃; pH=7.4; aq. phosphate buffer; Enzymatic reaction;79.1%
4336-39-4

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 6h; Inert atmosphere; Schlenk technique;81%
With ammonia In methanol at 20℃;
With Amberlite IRA 120 H+ In 1,4-dioxane; methanol14.1 g
1391764-47-8

5-(2,5-dimethoxythiophenyl)-5-methyl-5,6-dihydrouridine

1463-10-1

5-Methyluridine

Conditions
ConditionsYield
In water for 0.0666667h; Photolysis;78%

Ribosylthymine Chemical Properties

Molecule structure of 5-Methyluridine (CAS NO.1463-10-1):

IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 
Molecular Weight: 258.22796 g/mol
Molecular Formula: C10H14N2O6 
Density: 1.576 g/cm3 
Melting Point: 183-184 °C(lit.)
Index of Refraction: 1.618
Molar Refractivity: 57.43 cm3
Molar Volume: 163.7 cm3
Surface Tension: 75.9 dyne/cm 
Storage Temp.: 2-8 °C
XLogP3: -1.6
H-Bond Donor: 4
H-Bond Acceptor: 6
Rotatable Bond Count: 2
Tautomer Count: 3
Exact Mass: 258.085186
MonoIsotopic Mass: 258.085186
Topological Polar Surface Area: 119
Heavy Atom Count: 18
Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChI: InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1
InChIKey: DWRXFEITVBNRMK-JXOAFFINSA-N
EINECS: 215-973-9
Product Categories: Pyridines, Pyrimidines, Purines and Pteredines; Miscellaneous Biochemicals; Nucleotides and Nucleosides; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Nucleotides

Ribosylthymine Safety Profile

Hazard Codes: VeryT+
Risk Statements: 26/27/28 
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 24/25 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Ribosylthymine Specification

 5-Methyluridine (CAS NO.1463-10-1) is also named as Ribothymidine ; Thymine riboside ; Uridine, 5-methyl- . 5-Methyluridine (CAS NO.1463-10-1) is white powder. The stability of 5-methyluridine under standard temperature and pressure (STP) is very high.

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